Embracing Failure (On Purpose!) From a young age my loving dysfunctional family, placed unnecessary mental hurdles in front of any expressed asspirations, goals, or actionable curiosities. These were contrived in advance of any action having been attempted. So for me, failure was a tickle in the back of my mind as something to avoid, to the point of don’t try to hard or don’t try at all. The idea of failing became the feeling of “not good enough.” Thank goodness for adolescence and the attitude of “Just do it!” range louder. It helped that was also the new Nike slogan and you saw it everywhere. No one was there to help me understand that trying something and failing was part of the learning process. Figuring out what does not work, trying again, until you figure out what does work. At first it felt like just trying would result in failing and I would be choosing to do that on purpose. With time problems became challenges and now, when I’m feeling stuck, or things are not moving along the way I would like I shake it up and try something new to start failing at – not in a self-sabotaging way, but as an experiment—to see what would happen if I gave myself permission to mess up, stumble, and try again. I’m now addicted to challenges and what I learn in the process!
1. The Setup: Planning to Fail
A simple plan: pick something low-stakes and approach it with an open mind. I decided to try painting—something I’m objectively not great at. My goal was not to create a masterpiece but to explore what happens when I take the pressure off.
- Expectation: I’d make a mess, laugh it off, and toss the canvas in the closet.
- Reality: I made a mess, yes, but I also found joy in the process. I played with colors, splashed paint without worrying about perfection, and created something unexpectedly beautiful.
Ah-Ha Moment: When you strip away the need for a perfect outcome, the experience itself becomes the reward.
2. The Surprising Benefits of Failing on Purpose
When I let myself fail, a few unexpected things happened:
- I Feel Free: Without the pressure to succeed, I feel lighter. Each brushstroke isn’t a test, just an experiment.
- I Laugh More: When my first attempts at something new go awry, I genuinely laugh—and that feels like a win.
- I Learned Quickly: Without the fear of getting it wrong, I try more ideas and treat the experience as more of a challenging 3D puzzle. Learning is winning!
Ah-Ha Moment: Failure, when embraced, is a playground, not a punishment.
3. Applying This ‘Failing Forward’ Mindset to Real Life
After adopting a ‘Just Do It’ attitude, I noticed it became easier to try the next new thing that came to mind and started to apply this mindset in everyday situations:
- Cooking: I Pinterest my way around the world, trying things I’d never think to do. My family and friends love the variety… even when its a swing and a miss. Last night we had spring roll salad… sooo good!
- Trying New Hobbies: I change up my hobbies every few years. I love catching a spark of interest, the preliminary research, testing the waters, and then jumping in! Right now I’m sail racing and playing pickleball. Two years ago I was still in road cycling and gardening. I still do them on ocation, though not more in the background.
- New forms of income: I’m never short on some sort of project being in the works. This whole thing with Mindful Madness is me doing my thing while sharing it with the public. Usually I share with those in my immediate circle… so this is d-i-f-f-e-r-e-n-t.
Ah-Ha Moment: Sometimes, the best wins come from the freedom to fail without judgment. And if someone is judging, it says more about them than you. Just Do It!
4. How to Try Failing on Purpose (And Actually Have Fun)
If this sounds like an experiment worth trying, here’s how to do it:
- Pick Something Low-Stakes: Start with an activity where the outcome doesn’t matter much—like doodling, baking, or learning a silly dance. I’ve tried shuffling myself. lolz
- Set an Intention to Fail: Tell yourself upfront that this is just for fun. The goal is the experience, not the end result.
- Celebrate Every Misstep: Instead of criticizing yourself, find the humor in every flop. Laugh at the burnt cookies, the offbeat dance moves, or the wobbly new hobbies.
Ah-Ha Moment: When failure is the goal, every mistake is a win.
Conclusion: The Power of Failing on Purpose
Failing on purpose turned out to be one of the most freeing things I’ve ever done. It took the sting out of imperfection and turned life into a playground instead of a test. So, what will you try (and intentionally fail at) next? Who knows—you might just find a win hidden in the experience.
